Under Her Spell
by Jewannaman
Summary: AU. Multi-chap fic post 1x04. Dan's dating Serena, but Blair Waldorf is ruining it for him.
1. Prologue

_So this is my first attempt at a multi-chapter fic. It is written for post 1x04, Chuck and the limo never happens. Blair finds out about Nate and the business deal and leaves him. Everything from that on is completely AU. A lot's happened since 1x04 and this AU world. Blair lost her virginity to Nate before they broke up. Blair is still mad at Serena for sleeping with Nate because I refuse to believe Blair would forgive Serena that easily. So to sum up, their relationship is iffy. You will have to fill in the blanks for everything else. Also, expect a good amount of smut in this fic ;)._

_I apologize for the length of this chapter, but it's the prologue, I promise the future chapters will be longer. _

_Disclaimer: I don't own the characters_

* * *

Losing his virginity to Serena wasn't as great as he expected it to be. He wasn't even sure Serena came. How do you tell if a girl fakes it? Dan looked over to a panting Serena who looked pretty happy while lying on her bed. Oh well, it was good enough for him.

He sat up and pulled up his trousers. After giving her a quick goodbye, he left Serena's penthouse in the hopes of not running into Bart or Lily. Unfortunately, a smirking Chuck caught him leaving. Chuck congratulated him on entering where many had already been. Everyone said Serena's been around, but he always pushed the thought away.

He headed home and avoided Rufus for the night. Just as he fell on his bed, he received a text from Jenny about getting in some trouble and needing help. A groan in annoyance escaped his lips and then he went down the fire escape.

Jenny was over Blair's so he took the subway to her penthouse. He was reminded of why it was a bad idea for his baby sister to be spending time with Blair and her minions.

He arrived in Blair's living room to see her drinking a martini and sitting on the small white sofa. It was surprising to find her alone, but he gathered all the girls had left already.

"Your sister can't handle her liquor cabbage patch" Blair said and her sparkling pink lips curved.

It becomes clear Blair was the one who used Jenny's phone to text him. It seems she was tired of playing with his sister for the night. After spending weeks with Blair, he's beginning to think the girl in the hallway was just a figment of his imagination.

"Where is she?" Dan asked and his brown eyes scanned around the living room.

"Passed out in the guest bedroom" Blair answered looking over her nails and seeming uninterested to his presence. Her eyes then left her nails and met Dan's eyes.

"Serena told me what happened last night with Nate" Dan slid his hands in his pocket

For some reason, he wanted to see if she was okay because it felt like no one else ever asked her how she was doing. Before Serena came into his life, he knew how it felt. If he looked past her bitchiness, and cold exterior, he could relate to her.

A frown appeared on her face and she covered it with her flute. It was surprising to see Nate pull such an ass move. Nate seemed like a very nice guy, but then he was also the guy who kissed Jenny thinking she was Serena. He was new to the Upper East Side so it was still taking him time to become accustomed to the backstabbing that occurred in this world.

Blair bent her knees so he could sit on the edge of the white sofa. His eyes went straight to hers because that was the only part of her he could ever read. They were soft and there was a glint of pain.

"You can't force a relationship. He hasn't shown any indication of being in love with you. He might say it, but it doesn't seem to ring true in my eyes" Dan reached out and touched her leg that was covered with stocking.

Blair's nod seemed to show an indication of conceding.

"What a waste of 10 years" Blair said softly and laughed a little to herself

They let their eyes stay in each other's gaze for what felt like a long minute, but then she broke his stare and brought up his sister's name to change the subject. Dan followed her upstairs, but they went to her room first to pick up Jenny's cellphone.

It was the first time he set foot in her room and he noticed her cabbage patch doll on a shelf. He went straight to it and ignored the protests he was hearing from Blair.

Dan grabbed the doll. "What's her name?"

"Holly"

He spun around to face her. "I can't believe you ridicule me for owning Cedric"

"Give her back Humphrey" Blair reached for it, but his arm was too long for her get around.

Blair was pushing and jumping until Dan grabbed her along her waist and pressed her closer unintentionally. She was too close for his liking and he could smell the trace of alcohol from her breath. Dan swallowed hard as her eyes were set on his lips. Her shiny pink lips were tempting him to lean in, but the scent of alcohol was pushing him away. In the end, it didn't matter because she leaned in and pressed a soft kiss on his lips. It took a while for him to grasp what was happening and then he finally began to move his lips with hers.

The back of his mind was telling him that she was going to come to the realization that her lips were on someone from Brooklyn and he was going to receive a slap for it. But then he heard a whimper from her and considered the fact that she might be enjoying it.

_Serena_

Serena flashed his mind and pulled away. His eyes were widened while she looked lost as her fingers were on her lips.

Dan was in shock. It was too much and he couldn't handle it. He quickly gathered his thoughts and grabbed Jenny's cellphone. He didn't even say bye and Blair didn't protest. She just stood in her room looking to be in deep thought.

After he left Blair's penthouse with Jenny in his arms, he had only three different options on what just happened.

A.) Blair's attracted to him and that led to the kiss. At least he hopes that's the reason because it was the only reason he kissed her back.

B.) Blair was drunk and she let curiosity affect her better judgment which he wouldn't mind because they could just pretend it never happened and he could be with Serena.

C.) Blair's using him as some plan for revenge against Serena which makes him feel like an idiot.

He thought option C was the most likely scenario, but it's impossible to tell when it comes to Blair Waldorf.

* * *

_So they kissed, but that doesn't mean they'll be dating anytime soon. This story is sort of wild and I think after what happened with Dair, we need a good old dair affair fic. Unfortunately, it's season 1, so sorry for that._


	2. Chapter 1

_Reading the reviews was a blast so thank you for them. As for the story, I'd like to explain the direction I'm taking these characters. I'm planning on staying true to the Season 1 route, meaning all the characters will be on the path season 1 created for us. I think season 2 began changing all the character's traits, especially Chuck and Nate. Dan on the other hand will be more like Season 3 and on where he wasn't as judgmental._

* * *

After Dan snuck Jenny back to the loft, his eyes closed but the images of kissing Blair wouldn't allow him any sleep. The fact that he felt something was troublesome. He was dating Serena and pursuing anything with Blair would be pure inanity. At the moment, the Queen Bitch of Constance was most likely coming up with her demands to blackmail him with. Blair's the type of girl who would sleep with him, take a picture, and then send it to Gossip Girl just to stick it to Serena. There was only one solution, and that was to pretend the kiss never happened.

Pretending the kiss never happened became difficult when he dreamed about her because there were now officially images of Blair in compromising images flashing through his mind. He rubbed his forehead and groaned in annoyance.

* * *

Having breakfast in the kitchen wasn't any better since he had to witness Rufus and Jenny yelling at each other. His dad caught on about Jenny breaking curfew and it shifted Jenny to the defensive. The argument led him to spree from home and leave for Serena's. Hopefully, a full fledge make-out session would do the trick and the kiss would be soon forgotten.

He left for Serena's, but instead of making out, he was stuck helping Chuck and Serena on their calculus homework. To make matters worse, Nate joined them which meant it would take him twenty minutes just to explain a problem to Nate. Nate kept asking for a break while Serena kept slapping Chuck's hand off her ass.

He gave into Nate and followed them to the terrace to watch them smoke.

"You do know we won't be able to get any work done for hours now" Dan said

"That's the plan" Nate smiled and passed him the blunt.

"No thanks" Dan replied and shook him off with his hand

Smoking might have been something that was common and fun in the Upper East Side, but losing brain cells wasn't something he considered a good time. After raving through Serena's fridge, they were left with playing Halo. Unfortunately none of them had a shot playing against Serena. There was something hot about a girl being good at video games.

Serena asked him to stay over for dinner and he agreed. Watching Bart and Lily converse made him cringe, but he enjoyed the sly comments by Chuck at the dinner table. It was the first time he had some alone time with Eric, and he liked the blonde boy. Eric wasn't like the other kids from the UES.

* * *

He reached school and headed for his first class. It had been a day since he had thought about the kiss and considered that it might have been meaningless after all. Heading for Mr. Bryant's, he smacked himself upside the head with his hand once he realized he would have to stand outside the hall of the classroom with Blair. Since his history class was his first class in the morning, it would mean the door to the classroom would be locked and they would have to wait for Mr. Bryant to come and unlock it. Every morning, he would stand outside the hall and listen to Blair's bitching and critique's while Nelly Yuki would be breathing on his neck.

He hadn't spoken to Blair since the kiss and couldn't help but feel awkward having to see her again. As he turned the corner into the hallway of his history class, he saw Blair's eyes on him while her hand was on her hip and she was cocking a brow. Her lips were curved into a hint of superiority, but it could also be considered alluring to some, or maybe it was just him. His throat tightened and he loosened his tie so he could breathe easier. Of course she looked as perfect as ever and he was in agony with her decision not to wear any leggings or tights.

"Hey" Dan nodded his head up slightly as an indication of _what's up_.

He leaned his shoulders against the cool lockers because there was something more comforting about that.

"Cabbage Patch" Blair smirked and rose her eyebrows as she her eyes scanned from his feet to his face.

Dan rolled his eyes in response

It became obvious she was going the route of pretending the kiss never happened, which was fine with him since she was the one to kiss him. If there was one thing he knew about Blair, it was that having the upper-hand was everything to her. Unfortunately for her, he had the upper-hand.

"Should I be expecting you to join us this weekend" Blair asked with a hint of curiosity in her eyes

"Join you for what?" Dan's brows furrowed

"We're going to Cloud Nine on Saturday" Blair said as if it was the most obvious thing in the world

"It's Monday. How about you ask me Friday?"

He already knew why she needed to know right now, but he liked to annoy her. Blair always liked to plan things ahead so she could work things out in her head. She was probably had a scheme ahead for this weekend and needed to know every little detail, like who would be joining them.

Blair pursed her lips and smiled sweetly. "Since you have no friends, I'm going to assume you'll be joining us"

"Actually, I might choose to watch a movie with Vanessa instead" Dan told her and slid his hand in his pocket.

"I don't think Serena would be happy with you spending time with Vanessa, who is clearly in love with you I might add"

Dan tilted his head to the side and smirked. "Are you sure you aren't talking about yourself?"

Blair's lips curved slightly and it looked as though she enjoyed his comment. "Wow, Dan Humphrey has some wit. You've officially just become more interesting"

Her flirting caught him by surprise. Either, like him, she felt something after the kiss, or she was up to no good. She was a mystery but that was what made her so fascinating. She wasn't like any character from novel's he's read in the past and he hadn't met anyone like her. She was unique and that was something he liked about her. It made his fingers itch to begin writing notes in his moleskin.

His heart was pumping faster and faster when they locked eyes. There was intensity in her eyes that he had never seen on her before. She licked her lips and it only made her lip gloss glisten more. The chatter coming from the crowd waiting outside the class was ignored and it felt like the only thing he could hear was her breathing. He didn't even know how she had gotten so close to where all he could smell was her Chanel No. 5.

"Hi Dan"

The moment was ruined and he broke their gaze to look over his shoulder to see Nelly Yuki behind him. Nelly had large black framed glasses which hid her beauty. She wasn't the most gorgeous girl in the world, but if someone helped her do her hair and gave her contacts for her eyes, he could see her being pretty.

Blair scrunched her nose in distaste, but he ignored her rude behavior and turned around to talk to Nelly. At this point, he wanted to avoid trouble and speaking to Nelly was exactly what he needed. This thing with Blair was getting dangerous.

* * *

The past week had been filled with pure anguish for Dan. It felt like Blair was purposely torturing him. She would make any excuse to touch him, like putting her hand on him when he would crack a joke or how they slide through the crowd in lunch but she would make sure their pelvis's met as they squeezed through. He even noticed her hiking her skirt up to show her garter belt in History class. Blair had a plan and the only person he could to speak to about it was Jenny. No one knew Blair as well as Jenny did.

On Friday, the day before he was supposed to go out with Serena's friends, he told Jenny everything and asked for her input on the situation. He instantly regretted confiding in Jenny when she fell on the floor of his bedroom and began laughing.

"You think Blair likes you?" Jenny asked, trying to quash her laughter

"She kissed me" Dan answered

"She was drunk" Jenny pointed out and raised her brows. "Okay, seriously, you're just seeing things because you're Humdrum Humphrey to her"

Dan rolled his eyes. "Do you think she has an ulterior motive then?"

"If what you say is true, then I wouldn't put it past Blair to try to get in-between you and Serena" Jenny replied and shrugged her shoulders. "Think about it, they date for 10 years, and then Nate sleeps with Blair's best friend and falls in love with her in the process"

Dan nodded in agreement. "Yeah, I think they would still be together if it wasn't for Serena"

"Exactly"

"Thanks for the help" Dan said

"No problem" Jenny stood up and patted his shoulder before leaving his bedroom

Because it was Friday, his phone was filled with texts and missed calls. Serena had really changed his social life. He chose to ignore them and spent the night writing on his desk with ear buds in his ear. Lately, he had loads of inspiration. It was much easier to write about Blair when compared to Serena because Blair was more interesting. There were layers to her while Serena was the prototypical fun blonde. Serena's story had been written before, but there was only one Blair Waldorf.

* * *

Dan woke up right before noon. After having breakfast, he left for Nate's because according to Serena, it was necessary he hang out with the guys before they leave for the nightclub. He went to the Archibald's townhouse to be greeted warmly by Mrs. Archibald. She led him to Nate's room and found him to be using Facebook.

Nate looked up. "Dan. How's it going?"

Dan sat at the edge of Nate's bed. "It's good"

"How come you don't have Facebook?" Nate asked with his brows wrinkling

"I don't know to be honest. I guess it's because I've always been kind of an outsider" Dan told Nate

Nate nodded in understandment. It was weird to be alone with Nate since they both knew he was in love with Serena. Nate broke the awkwardness by showing him Facebook profiles of their group of friends. Nate told some humorous stories and they laughed together. It was nice for once not to be treated like an outsider.

Soon after, Chuck joined him and that meant they had to go for a ride in his limo so Dan could watch them smoke. It was surprising how much they smoked and he could tell it affected Nate more than it did Chuck.

"So this must be pretty awkward for you two, seeing as how you both are in love with the same girl" Chuck said with his trademark smirk.

It was just like Chuck to play two people against each other. He seemed to enjoy pushing people's buttons.

No one said anything and the limo fell quiet. It wasn't the response Chuck was looking for and realized he had ruined Nate's high.

Chuck sighed and looked across to Dan. "I wouldn't worry too much about it Daniel. I'm sure Nate will be fine."

Dan wanted to change the mood so he decided to get a better idea of how things worked in the Upper East Side.

"How do you guys plan on getting in Cloud Nine? Are we using fake I.D.'s because I don't have one" Dan asked

Chuck looked at Nate with a small smile. "No"

"Then how?"

"I'm Chuck Bass" Chuck held a smug grin and shrugged his shoulders.

He had a feeling he would be hearing that a lot

* * *

His mind was on the cusp of exploding as he sat in Chuck's limo. People were drinking champagne, laughing, and some were even dancing in the little space that allowed it. It felt like these people lived in another world and he understood why they acted like they owned New York. They were spoiled with being able to have everything.

Serena was on his right and drinking from a flute while Blair was on his left holding a smirk. When he looked at Serena, he saw an angel that represented kindness and affability. When he looked at Blair, he saw darkness, which was tempting and appealing. He could see himself becoming infatuated with it and maybe even losing himself in the process. But there were also these moments when he would see the Blair hiding behind her wall and there was nothing more special than being able to experience that.

When they entered the VIP room, he was left scratching his head at the amount of alcohol Serena had consumed. He decided to take the sober route while the others decided to get wasted. Unlike the others, Blair drank conservatively, rolling her eyes at everyone's behavior.

Serena kept insisting they dance but dancing was never his thing. Her persistence didn't win out and Nate had to jump in. He told them he didn't mind if Nate danced with her and they left the table for the dance floor, where he was left alone to sip from his iced water.

Blair came back from the bathroom and slid into the booth, nice and close. She raised her brows as she looked over his appearance and he was getting really tired of her superiority act.

"You don't seem very comfortable" Blair said and began scooting closer to him while holding her glass of gin and tonic. "This doesn't seem to be your type of environment"

"Well apparently it's Serena's so…." Dan trailed off and shrugged his shoulders looking away

Blair smirked. "It doesn't seem like Serena's little experiment with you is working"

"I think its fine" Dan disagreed

Here it was, Blair was ready to play. She had him at a moment of weakness and was ready to put ideas in his brain. What Blair didn't realize was that he wasn't stupid enough to fall for her tricks.

"Really" Blair said sounding intrigued. "What do you even like about Serena?"

And that was Blair's first mistake. He knew how insecure she was about Serena and it was the perfect moment to pounce on her question which would push Blair off his case.

"Well" Dan mulled it over. "She's has long tan legs. Blonde hair that smells like heaven. She's actually the most beautiful girl I've ever set my eyes on. Not only that, she's a genuinely good person. She doesn't like to hurt others and if she does, it's not on purpose" Dan explained leading Blair to narrow her eyes at him. "Also, I'd like to add that she's really fun to be around"

Serena had many flaws as well, but he knew Blair never saw them or she did, but she didn't think much of them.

"Okay, so she's perfect" Blair acknowledged as she shrugged her shoulders. "But the more important question is what is she doing with you?"

He wanted to chuckle because this girl never gives up. It was extremely difficult to inside Blair's head. He had no idea what she was trying to do.

A smug grin formed on Dan's lips. "I'm good looking. Some would even say irresistible"

She rolled her eyes but he saw the smile she was biting back. She rarely smiled, but when she did, it was his favorite because he knew he must have done something special to receive that smile.

He followed Blair's eyes to Serena grinding against Nate. "She seems flawless doesn't she?"

"To some" Blair answered

Dan's lips curved into a smile. "The thing is, I find flaws really attractive"

"Shut up" Blair waved him off but smiled

"It's true. I think it's what makes a person relatable" Dan said holding a smile and meeting her soft brown eyes. "In my eyes, you eventually fall in love with someone because of their flaws, whether it's a friend or lover"

"You really believe that?" Blair asked softly

Dan nodded. "I do"

There was something about Blair he just got and with the look she was giving him, it felt like she just came to that conclusion as well.

He slid off the booth and put his hand out. "Would you like to Dance?"

Blair gave half a smile and placed her hand on top of his

* * *

Serena had drunk too much and was getting hard to control. They had to help her into the limo and it was scary to see because it was the first time he had ever seen someone that smashed. Chuck's limo pulled over to Blair's building and he helped Serena up to Blair's penthouse because they didn't want Lily to see her in this state of mind.

After changing Serena's clothes and tucking her in, he placed a glass of water and two pills of aspirin on her bedside. He then brushed the strands of hair covering her face and pressed a soft kiss on her forehead before stepping out of the guest bedroom. From the way Blair, Chuck, and Nate were acting, it was common for Serena to be this drunk.

He reached the foyer and saw Blair sitting in the living room and flipping through a magazine. She glanced over and stood up once she saw him.

"Would you like something to eat or drink?" Blair offered walking towards him

Dan slid his hand in his pockets and looked down to his feet. "No thank you. I should be going"

It was strange being alone with Blair and the quietness surrounding them was unsettling. The nerves he was feeling was something he never felt around Serena.

"Are we ever going to talk about that night?" Dan asked

A smirk formed on Blair's lips. "I was wondering when you were going to bring it up. I'm a bit surprised it took you so long seeing as how you like to talk"

Dan swallowed, feeling something stuck in his throat. "Did you feel something?"

"What do you think?" Blair whispered tilting her chin up to meet his eyes.

Her small hands slowly crept up to his chest and he tilted his head to meet her lips. Kissing Blair felt completely different from kissing Serena. It was more exciting and he never wanted to open his eyes. She gripped onto his shirt tighter than Serena would and her lips told him the whole story.

Somehow, his back landed on the wall of her beneath the railings of her staircase and her lips moved to his neck. Everything was going too fast and before he knew it, the first couple of buttons from his shirt were unbuttoned. Blair was aggressive and that was new to him.

He could have let her finish unbuttoning his shirt, but it was the wrong thing to do, especially with Serena upstairs. It's really fucked up and it led him to stop moving his lips with hers.

"What's wrong" Blair asked breathing heavily as she pulled away

"I'm in trouble" was all Dan said and saw a devilish smile form on her lips. "I have to go"

He squeezed his way out of her grasp and headed towards the elevator. He then pressed the elevator button and waited for the elevator to come. When he looked back to the foyer, he saw her eyes on him and she was biting her lower lip.

What had he gotten himself into? He was officially in-between Serena and Blair now, and from what he's heard, it's a dangerous place to be.


	3. Chapter 2

_Good lord, the reviews were a pleasant surprise. I'm happy you guys are enjoying the story. This is a fast update, but only because this chapter isn't as long as the others._

* * *

"I've never felt this way about anyone" Serena told Blair as they sat on the MET steps.

Serena glanced over to her friend who was poking at her fruit bowl in her well matched skirt and blouse.

"Hmm…"Blair pondered and placed her fruit bowl on the side. A smirk then formed on Blair's lips. "Are we speaking of three little words eight letters type of feelings here?"

Serena nodded hesitantly, not sure if she wanted to hear Blair's reaction.

Blair scrunched her nose in distaste. "Oh S. Him? Really?"

Serena knew Blair would never approve of Dan, but being in love was new to her and it was something Blair had experienced before.

Serena smiled and shook her head. "You wouldn't understand"

Blair placed her hand on Serena's thigh to catch her attention, leading Serena to glance back over to Blair.

"I may not understand your fascination with him, but I do know a little something about those three little words and you should never be the first one say it," Blair said which led Serena to roll her eyes. "Roll your eyes all you want, but having the upper-hand is the most important thing"

"Dan's not like that. He doesn't care about those sorts of things"

"There all the same S. Humphrey isn't any different" Blair said and pursed her lips.

* * *

Listening to the Postal Service, he never thought he would be that guy. The guy who listened to music and stared up at the ceiling contemplating what he should do. It was something he saw in the movies or TV shows, but it's actually happening to him. He was never a person who was a fan of the dramatics and that's why he knew he had to resolve this issue with Serena.

He heard feet landing on the floorboards of his room and looked over to the window to see Nate and Chuck enter his room by using the fire escape. Nate's lips were curved slightly in his green v-neck cashmere sweater while Chuck was in a button down with a long scarf wrapped around his neck.

"What's going on" Nate greeted

Chuck looked over his room and played with his scarf. "Very teenage angst Humphrey" Chuck commented on his room.

Dan sat up and straightened out his T-shirt. "What are you guys doing here?"

"Let's go for a ride" Nate offered and gave him a charming smile.

"It's Thursday, we have school tomorrow" Dan said

"We'll be back in time for you to meet your curfew" Chuck answered with a smirk

Nate walked over to his closet and began scanning through his wardrobe making Dan feel a little self-conscious. Nate grabbed a hold of his orange fluffed out tube vest.

"What the hell is this?" Nate asked raising his brows and holding it in front of Dan.

Dan shrugged his shoulders. "I was a fan of Back to The Future growing up"

"Put it on"

Dan shook his head. "No"

Nate nodded. "Yes"

Nate won out and they left out of the fire escape and headed for Chuck's limo. These kids smoked way too much.

"Are you finally going to join us for a smoke tonight?" Chuck grabbed his attention as he was walking towards Chuck's limo.

"Like I said before, it's not for me" Dan replied

"You're gonna have to get it out of your system at some point" Chuck reasoned

Dan decided to give in because he was getting tired of them asking him, but felt he was conforming to the UES. It was a difficult internal battle, but he was young and he thought Chuck was right, he would experiment in college anyways.

* * *

Blair was looking over herself in the mirror, making sure everything was perfect. Going out with Serena always made her feelings for perfection heighten. She looked at the minute flab under her arms and concluded she could still lose some weight.

"Have you heard?" Isabel asked sitting on the edge of Blair's bed.

Blair turned her body to face the girls on her bed. "Of course I've heard. I'm her best friend"

Katie's face scrunched in disgust. "Serena Van Der Woodsen's first love is Brooklyn"

Isabel laughed. "I know, we all thought it was some experiment"

"I think it's just some ploy to get a rise out of Lily. We all know she'll dump him when she's become bored of this Romeo and Juliet fantasy that's playing out in her head" Blair added and smirked.

Blair heard Jenny murmur something quietly to herself and the other girls took notice.

Blair arched a brow. "Excuse me" Blair challenged Jenny

Jenny stood from the bed and met Blair's eyes. "I think my brother has a good heart, and Serena knows that. But if you don't see it, then it's your loss"

Jenny then stormed out of the room, leaving Blair speechless and frozen. Blair couldn't believe the gall on little Humphrey and how rude it was to challenge her in front of everyone. Blair gathered her thoughts and excused herself from Katie and Isabel.

Hurrying down the staircase, she caught Jenny just in the nick of time as the elevator doors were just beginning to open. Blair called out Jenny's name, leading Jenny to stop abruptly and spin around to face her as she approached the young blonde.

"I'm sorry Blair, but I can't listen to you speaking about my brother that way" Jenny told Blair and placed a hand on her hip.

Blair couldn't lie, she was impressed with the girls courage. It was uncommon for her minions to stand up for themselves.

"It's just gossip Little J" Blair explained looking over her nails.

Jenny tilted her chin high and proud. "Yes, but I'm from Brooklyn too and I'm not going to sit around listening to that type of talk"

"Fine, you can leave" Blair said as her eyes drifted off of her fingernails. "I'll let it go this time, but don't ever speak to me that way again"

Jenny nodded but before she could step into the elevator, Blair grabbed a hold of her arm, leading Jenny to glance over to Blair.

"Don't tell Dan" Blair said quietly and confusion mixed in with shock was written all over Jenny's face. "Please"

Jenny's mouth opened and Blair rolled her eyes.

"Okay"

"I'm sure you can put the pieces together. So I'm trusting you" Blair confided in Jenny

The girl looked scared and Blair knew she was asking a lot, but there was something she liked and trusted about Jenny.

"Of course, this stays between us" Jenny confirmed and gave her a reassuring smile.

* * *

Dan had a case of the munchies as he stared outside Chuck's limo and passed restaurants. He licked his lips at the thought of a shawarma roll up in his hands.

He glanced over to Nate and figured the blonde could give him some useful information and help him with the conundrum he was currently in.

"What was it like to date Blair?" Dan asked

"I don't know" Nate's brows furrowed thinking about it. "I just remember her bossing me around a lot"

They laughed together and he concluded that was the most he could get out of Nate. Which was fine because Nate had already given him more than enough. Everything about Nate rang _cool_. From his slick backed long hair, to his perfect smile, to his laid back personality.

"I do miss her" Nate confessed

"Then why don't you tell her" Dan asked, not knowing how to feel about the prospect of Blair and Nate dating again.

Nate's lips curved into a smile and he looked over to Dan. "Because I'm having too much fun being single"

Nathaniel Archibald had become quite the player after Blair had broken it off. He had been spotted with numerous girls, but none were able to hold his attention.

"You should try it sometime Humphrey. Especially now that you've lost your V-card" Chuck said with a smirk. "Although I can't imagine anyone being better than Serena"

"Sure" Dan said because he didn't have a clue of how else to respond to Chuck's remark.

Dan's phone vibrated and he had received a text from Serena asking him to meet her at Central Park tomorrow before school.

* * *

_Good Morning UpperEastsiders,_

_**D **__and __**S**__ spotted having a Central Park picnic before school. A little birdie told me __**S**__ is ready for those three little words eight letters. Looks like __**S**__ has finally been tamed. _

_You know you love me_

_XOXO,_

_Gossip Girl_

Blair felt a little hurt after she read the Gossip Girl blast. But like she told Serena, Dan wasn't different from any other boy. He knew he could have both and he was taking advantage of it.

There was no way she was going to let Dan Humphrey ruin her special day. It was early Friday morning and she could hear her mother chattering it up with her assistants. It's the one day all the attention would be on her but her mother didn't get the memo.

Her mother bought her a new sparkling necklace, wished her a happy birthday, and left with her boyfriend for a romantic weekend away from the city. She was still not going to let anything affect her mood.

She left for school and heard happy birthday ringing through the halls. She couldn't fight off the smile on her face because it was her day. There were little whispers in the halls were about her and her birthday party which was exactly what she wanted. Her mood was bright until she reached Mr. Bryant's class and had to wait outside in the halls with Dan by her side. Even as she tried to pretend he didn't exist, she couldn't help but notice something was off. He was quiet and a little sad which was very unlike him. He didn't seem to mind the fact that she was ignoring his existence.

After field hockey practice, she left the school with her minions and began ensuring everything was nothing less than perfect for her party. She had booked a perfect venue for her birthday party. Unfortunately, she wasn't able to serve alcohol for the party which was a bit of a downer, but she still had her dress. It took her a week to pick out the perfect dress, but when she saw that black dress, she knew it was the one she would wear.

As the limo took her to the location of her party, she was getting irritated with the silly pop music playing, but she put out a fake smile because all the other girls seemed to be enjoying it. She rolled her eyes to her minions taking shots of vodka and trying to get a little tipsy before her party.

They reached the party and she let her minions out first before stepping out and enjoying the feeling of everyone's eyes on her. Chuck greeted her at the door as she stepped into the blue and red lighted party. As they walked into the party, he whispered some dirty things causing her to scrunch her nose. She decided not to speak with Chuck for the rest of the party.

She looked around for Serena who she hadn't seen for the whole day. Serena didn't even come to Field Hockey practice and she was getting worried.

Blair finally found Serena by the bar, ordering a non-alcoholic beverage.

"Hey" Blair said leading Serena to turn around to face her

Serena blinked. "Blair. Happy Birthday"

"Where have you been?"

"I know, I'm sorry B" Serena apologized as a frown appeared on her lips. "I don't know if I should tell you right now. I don't want to ruin your special day"

Blair tilted her head to the side and her brows furrowed. "You're making me worried S"

"I broke up with Dan"

Her heart froze in shock. She didn't see it coming because just the other day Serena was professing her love. She expected something like this to be posted on Gossip Girl but somehow Serena was able to keep it under wraps.

Serena smiled a little disbelievingly. "I told him I loved him and he told me he kissed another girl"

Blair's eyes widened and she swallowed nervously. The last thing she wanted in her birthday party was to have a fight with Serena in front of everyone to witness and post on Gossip Girl.

"Do you know who the girl was?" Blair asked hesitantly

Serena frowned. "He didn't tell me, but I'm suspecting it was Vanessa"

She was hit with a wave of relief that Serena hadn't figured it out yet even though there would be nothing more satisfying than having Serena feel what she felt after the whole Nate debacle.

"The funny thing is, I didn't want to break up with him. I want to be with him, but it feels like he's really confused right now so I'm just giving him some space" Serena added

Blair nodded and gave Serena a few kind words before departing and looking for Dan. She was surprised Dan told Serena the truth. He had Serena in the palm of his hand and he was willing to give that up because telling the truth was right thing to do. She couldn't think of anyone who would do the same thing Dan did if they were in his position.

_He really was different_

She walked around looking for him, but couldn't see him anywhere. She frowned at the thought of him not attending her birthday party.

She didn't have time to sulk as more and more people came and wished her a happy birthday. She played a good little hostess but didn't enjoy it as much as she thought she would've in the morning.

The lights to the venue dimmed and the birthday cake had arrived with candles lit. People began singing happy birthday and she knew it was time to blow out the candles. Just as she leaned down to the candles, her eyes caught sight of Dan on the other end of the table holding a small smile. He toasted his beverage up and she smiled before letting out a huff of air to blow out the candles.

After the candles were blown, the invitees cheered and clapped. The room's lighting came back and her eyes went to Dan who walked down the hall. She politely excused herself and followed him down the secluded hallway.

She found him standing by the employee's only room in a twill blazer. As she stepped closer, the music from her party faded and she was surprised to see him holding a moleskin in his hand.

Dan's lips curled into a smile as she approached him. "You're glowing"

"It is my birthday" Blair said

"The day you're not in Serena's shadow right?"

"Yeah" Blair confirmed softly as she tilted her chin up to meet his eyes.

"You were never in her shadow." His eyes went to the down to avoid her eyes. "At least not to me" Blair licked her lips and stared at his. "I don't really have a lot of money so this was the only thing I could give you"

His eyes moved up to meet hers as he handed the moleskin he was holding.

She traced her finger across the moleskin. "Thank you"

"Your bookcase is filled with some impressive literature. I didn't take you as a reader" Dan told her.

"So you wrote me a story?" Blair asked and stepped closer to press her chest against his.

"It's not finished yet but if you enjoy it, I might finish it" Dan said.

Blair raised her brows, looking hopeful. "Can you come to my place after the party?"

Blair bit her lower lip waiting in anticipation for his answer as their eyes stayed locked. Dan nodded leading her to break out a smile. She then stood on her tiptoes to press a soft kiss on his cheek before giving him the space to leave and head back to the party.


	4. Chapter 3

_Thank you guys for taking the time to review as they are the best way of determining how good a job I'm doing.  
_

* * *

Serena stepped outside the party and took the elevator. She asked around and had been told Nate was downstairs most likely getting high.

She spotted Nate in a secluded dark alley wearing a white coat jacket and holding a lit joint in his mouth.

"What are you doing here?" Nate smirked and his foot left the wall to go back in place on the wet cement road.

"I thought you might know where Blair is"

Nate pinched the bridge of his nose with his thumb and index finger. "She left"

The chances of Blair leaving without saying goodbye were slim to none. She pulled out her cellphone and found the clock striking past midnight. With the guests leaving, she had hoped Blair wouldn't mind spending her birthday having some cake and listening to her talk about Dan.

Archibald offered her a hit of his joint and she took it from his hands without thinking twice.

"There was some chattering going around of Dan being here" Serena said

She wished it were untrue because it would mean he had left without a goodbye and that was not what she wanted when she chose to break things off.

"He was here, we chatted for a bit, but he left rather abruptly"

She watched a slight curve to his lips as she let the smoke burn her lungs.

Serena's brows furrowed and she passed back the joint. "I'm surprised Dan was invited"

"Maybe Blair's the mystery girl" Nate teased in some good old fashion humor.

She wanted to join Nate and laugh at the idea, but it would be naïve of her to ignore the past two months of her best friend and boyfriend gradually getting closer, no matter how unlikely it may have been.

"Speaking of Blair, have you considered asking her to Cotillion" Serena inquired

"I don't think she would consider going with me" Nate answered

"You and I both know there is no one else she should go with"

Nate's eyes crinkled as he took the time to think it over.

"I'll think about it"

* * *

It's beginning to get frigid and winter didn't seem so far off anymore as the doorman to Blair's building let him in. After Dan promised Blair he would come over, he left the party and snuck back into the loft to pack a bag of clothes. Being punished for not coming home for the night awaited his future, so he decided it wouldn't hurt if he spent the whole weekend outside of Brooklyn.

It was dark when he set foot in the foyer. The lights in the living room were dim, making him even more tense. A slight curve to Blair's lips was formed when she saw him. Her lips were curved in a seductive manner and her skin looked delicious. All thoughts of Serena were forgotten because tasting Blair's creamy skin became a must.

The brunette was sitting on the white ottoman, legs crossed and holding a glass of liquor Dan couldn't make out. He noticed her change in attire. The black dress from the birthday party was gone and was replaced with a simple silk knee high red dress.

"I originally thought you were trying to break me and Serena up" Dan said and dropped his bag of clothes on the side of the doorway.

"And you're doubting that now because…?" Blair smirked and her well-toned legs sauntered over to him with the click of her heels.

Long gone was the Blair he spoke to at the party.

"Tell me Dan" Blair went on as her ruby red lips were tempting him to lean in. "How do you know this wasn't the plan all along?"

Dan grabbed a hold of her waist and pulled her closer, earning him a gasp from Blair. Her mouth remained open as his hands slid to her hips. He saw a little pink tongue dart out and he let his tongue play with hers before meeting her lips for an opened mouth kiss.

The noise of a glass shattering rung in his ears and Blair's arms wrapped around his neck. They somehow slowly landed against the wall next to the lit fire place.

Pressing soft kisses on her bare collarbone, Dan shrugged her spaghetti straps off to reveal a black La Fleur bustier and tight panties that made her camel-toe visible.

Dan's lips left her neck and met her eyes. A cry of protest escaped Blair's lips after his lips left contact unexpectedly.

"I really like you" Dan said softly and looked deeply into her eyes.

"I know"

"How do you feel when you're with me?" Dan asked leaning in closer to her lips with their noses grazing.

She brushed his lips with her fingers and kept her eyes connected with his.

"Exposed" Blair admitted softly.

"I think that's a good thing" Dan replied softly.

Her leg curled around his hip to tug him closer. With the little space he had to work with, he moved his hand all the way down to her panties.

He began gently rubbing the outside of her folds with his middle and index finger. She lost control and began grinding against him while their lips brushed.

She was in such a state of torture that he decided to give in and drive his fingers into her slickness, causing a satisfied moan against his lips.

Blair then left his lips and moved towards his ear.

"Take me to my room" Blair whispered seductively.

* * *

Dan's breathing was out of control as he stared at the ceiling in Blair's bedroom. He looked over to see Blair glistening from the sweat on her skin. Her eyes still remained dark and it looked as though she wanted more even though she was breathing irregularly.

The sex was different from Serena's. With Serena, it was milder. Blair was more demanding and it felt like she had expectations that needed to be met. Serena would giggle and laugh when she was beneath him, but Blair would dig her nails into his back and enjoy the pain she caused. Or she would hold a seductive smile when on top. That's the other thing, she disliked being in the missionary position.

He felt her hand reach out to pull him into a bruising kiss and he could sense she wanted more. It was still taking him time getting adjusted to her aggressiveness. She liked to bite, especially when they kissed, which was new, but it turned him on.

Spending the night having sex with Blair taught him a few things that turned her on. One was that she loved to talk dirty. It wasn't his thing, so he would let her do most of the talking. There were times he would choose to say a few lines of poetry instead and they seemed to have some positive affect on her. Confidence was another turn on, but that wasn't an issue for him after dating Serena. Of course the most surprising thing he learned was that she liked to be held possessively. She liked to be wanted and all these things were new to him. Blair was definitely different.

As her lips were moving with his lips, she reached across and grabbed his cellphone from the bedside dresser. His brows furrowed when she started looking through his phone.

"What are you doing" Dan asked.

"Checking up on you" Blair replied and acted as though she was doing nothing wrong.

Her intrusiveness was another thing he was going to have to get used to.

"Hmm…You have a lot of 80's music on this" Blair went on as her eyes narrowed.

"Well the 80's was a very underappreciated decade of music. Could you imagine going through middle school without a little Cyndi Lauper in your life?" Blair's arched a brow as she held an amused smile on her lips. "Don't pretend like you and Serena didn't dance around to _Girls Just Want to Have Fun_"

"Seems like the usual, Dylan, Dave Matthews, some Stones. I'm a little disappointed Humphrey. I was expecting more Indie," Blair critiqued and pursed her lips. Dan then noticed a devious smile growing on her lips. "Let's see what you've been texting Vanessa."

Dan sighed and rolled his head back.

* * *

Chuck Bartholomew Bass awoke past noon Saturday morning with a smirk. He felt the body next to him move and glanced over to see Dylan pulling his boxers up.

"Leaving already" Chuck said with lazy smile. "Not that I'm complaining. I find it refreshing"

Dylan chuckled as he began buttoning up his shirt.

"Right" Dylan said and looked around for his pants.

Dylan left and Chuck headed for living room to see Nate hitting a bong. There was nothing better to wake up to then a freshly packed bong for him to take a hit of.

"What are you exactly" Nate asked just as he slid the bong over.

"Whatever seems fitting for the night" Chuck answered

Nate looked over his phone and his brows knitted together.

"What's wrong?"

Nate's eyes went to Chuck.

"Gossip Girl hasn't spotted Blair anywhere since the party" Nate told him

The little fuck was beginning to understand how good he had it with Blair.

Chuck's lips left the bong. "Are we having regrets Nathaniel?"

"I was thinking about asking her to Cotillion"

Just what Chuck needed, his best friend being off the market. The past few weeks had been the best time he's had in years.

"How about we figure out what to do before your mother's party" Chuck said

"I invited Dan to that function by the way, so maybe we could do something with him"

A crease formed in-between Chuck's eyebrows. "What is this infatuation with Dan Humphrey?"

Chuck didn't like the cat from Brooklyn squirming his way into their world and he was going to do something about it.

* * *

They were sitting in Blair's large closet and going through her racks of shoes. Blair was trying to find the perfect heel, but Dan was making it difficult for her.

"We're only going downstairs to eat" Dan pointed out as he sat on the floor and waited patiently.

"This is going to be my attire for the day. I can't make some hasty decision" Blair replied and continued to try on different heels.

Her brows crinkled when she heard him chuckle. Sometimes it would be difficult to understand what he found so funny.

"I got a text from Nate asking me to come over to Chuck's"

"So go" Blair said as her focus remained on her heels.

"Oh"

She tried to ignore the pleasure she was feeling from the disappointment coming from his voice.

"Do you want me to come over later tonight?" Dan asked.

"If you want to" Blair answered coolly.

She had to play her cards right. One of her favorite sayings was _never show a man your cards_. If you want to keep a man, you have to keep them wanting more so they won't get bored of you.

Somehow, as she was going through her heels, she never saw Dan coming closer. He was now on his knees, only inches away and she could feel hot air on her neck coming from his mouth. Her strong posture was on the brink of breaking down.

When Dan's hand cupped her cheek, she was finished. Their eyes met and she bit her lip to try and hide how he was making her feel. He knew and it led to a smug grin forming.

His long cool fingers slowly slid under her blouse and on to her breast. Her mouth opened at the feel of him rubbing his fingers in-between her hard nipple.

Blair grabbed a hold of the back of his head and pushed him in for a hard kiss. She straddled herself on top of him and let out an excited yelp when he ripped her blouse open, buttons scattering all over the carpeted floor.

Once her panties were off, she slid into him and started riding him slowly, enjoying the feel of his tongue molding her nipple. He was biting and sucking hard which only caused her to moan louder. She felt so wanted and nothing had ever felt better.

The mark's he was leaving on her hips from his thumbs was only making her ride him harder. She suddenly felt his lips leave her chest and she looked down to a frightened Dan.

"Blair?" Serena called out.

Blair smirked and continued to move her hips as she enjoyed the thought of having sex with Dan while there was only a wall in-between them and Serena.

Blair leaned her forehead against Dan and grabbed a hold of the back of his head with both hands.

"Don't stop" Blair whispered as continued to move against him.

Dan didn't stop. Instead he kissed her and met her thrusts as Serena continued to call out her name.

As soon as she heard the elevator, her lips left Dan's and her moans grew loud with her climax threatening to erupt.

"I'm close" Dan said, breathing irregularly.

He slid his finger to where they connected and it triggered out a cry from her. She couldn't hold her release any longer and let go. Dan wasn't done, but she was having trouble moving and Dan could tell, so he picked her up and placed her on her back. Keeping both of her arm's above her head and hands intertwined with his, Dan thrusted into her hard and fast until he found his release.

A panting Dan stayed on top of her and she could feel him moving with her heaving chest. There wasn't any condom. It was just them, bare and connected.

* * *

Dan left Blair's with a pulled hip flexor. He took a taxi to Chuck's and was told he was invited to Mrs. Archibald's party. They had started speaking to each other two months before and had only recently begun texting. So when Nate invited him to his mother's party, it came as a surprise.

To get a suit for the party, he would have to go back to Brooklyn, which meant facing his father and having to be lectured on curfew. It was certain he would be grounded come Sunday, so he decided to make the most of his time.

Chuck had his own personal suite. One which included a pool table and large Jacuzzi out on the terrace. It seemed Bart didn't have a tight leash on his son and Chuck's friends benefited from it.

He entered the suite and played a little pool. Nate was friendly but there was a peculiar cold front coming from Chuck's direction.

Dan walked around the pool table and knelt down, trying to figure out the angles before he took his next shot.

"So Daniel, who's this mystery girl I've been hearing about? It must be getting pretty serious if you just spent the night at her place" Chuck said

A crease formed in-between Dan's brows. "How would you know if I was with her last night?"

Chuck smirked. "I just put two and two together. If you weren't in Brooklyn, then where else would you be?"

Dan blinked. "I was with Vanessa."

Nate looked confused. "You're lying. I was having sex with Vanessa last night."

_Shit_

He was screwed.

* * *

Blair took a breath after checking herself in the mirror, but her attention soon left the mirror and went to the sound of the elevator. She walked down the staircase and saw her mother coming in with some luggage.

"Mother, I wasn't expecting you until tomorrow" Blair said as soon as her heel landed on the foyer.

"Well yes, that was the plan initially, but then I received a call from my assistant and I must catch the next flight to Paris" Eleanor explained as she looked over the mail on the small table holding a vase.

"Interesting; Anyways, I should be heading for Nate's soon, so…" Blair spun around and almost reached the staircase.

"Blair" Eleanor called in a warning tone leading Blair to shut her eyes in fear and turn around. "Dorota told me something about a boy staying overnight"

"Well yes, but this specific boy is practically homeless, so some would say it was an act of charity" Blair spun the truth.

Eleanor gave Blair a stern look, not looking in the mood for jokes. "Who's the boy?"

Blair folded her arms across her chest and frowned. "Dan Humphrey"

Eleanor's eyes appeared as if they were on the cusp of popping out of her socket. "Serena's boyfriend!"

Blair sighed and looked down across her shoulder. "Ex"

"Oh dear" Eleanor knees weakened and she sat on the bottom of the staircase.

* * *

"Do you think he'll say something?" Blair asked before she tasted the ice cream on her spoon.

Nate lied, he never slept with Vanessa. Chuck and Nate planned ahead and tricked him into telling the truth, but Nate got an answer he wasn't expecting and it earned him a black eye.

Dan met her eyes from across the marble island in the kitchen. "No, but Chuck might"

His spoon dipped in the bowl they were sharing but he noticed the devilish smile on her lips. Her windows were covered with hard noisy rain in the back and she didn't flinch once to the sound of lightning striking. Instead, from what he could make out in the darkness, she seemed to be enjoying this whole problem they were in.

"Chuck won't say anything to Serena. He would rather blackmail us" Blair explained looking amused.

"You look like you're enjoying this" Dan said.

She leaned a little over the counter top, giving him a hint of cleavage from her unbuttoned blouse. "It's hard to worry when I think we'd make a good team"

He couldn't tell if she was doing it on purpose, but she was driving him insane. He found everything she did seductive. Her lips were voluptuous and it only reminded him of the previous night when they were wrapped around his length.

He dropped his spoon and rubbed his face with both hands. "I really can't think straight when I'm around you"

She laughed a little and it was music to his ears. He really loved her laugh. Lighting up her mood was always fun and he couldn't remember another time when he enjoyed someone's laugher this much.

"Tell me something about yourself" Dan said

"I'm a romantic" was the first thing she said.

Dan smiled. "But it's also important for there to be drama in your love story"

"Hence the reason I dropped the glass last night" Blair told him

His eyes narrowed at her accusingly. "I knew it was on purpose"

She giggled and he joined her with some light chuckling. Sometimes he forgot she was still a 17 year old girl. In the moment, she wasn't Queen B of Constance and he wondered if this was the side Nate got to see when they were alone because he couldn't understand why Nate wasn't into her at one point.

Soon, that smile of hers was gone and he was left with something difficult to decipher.

"My mom was here" Blair told him and fed him a spoonful of ice cream.

It was difficult to say if she knew what she was doing. He could've picked up his spoon that was lying on the side, but he shamelessly enjoyed her feeding him.

"What did she say?"

"She kindly reminded me I wasn't Serena" Blair pursed her lips and smiled, but it didn't reach her eyes. She shook her head at the thought of her mom. "None the less, my mother isn't the issue here"

"Then what is?" Dan asked.

Blair sighed and moved her curled fingers under her jaw, face propped up on the island. "Nate's very upset. Not to mention the fact the Serena will probably never speak to me if she finds out."

"I thought this was what you wanted"

"I wanted to hurt her as much as she hurt me, but then things changed" Blair replied and met his eyes.

Things did change. The kiss wasn't supposed to lead to this.

"Do you love her" Blair asked softly.

"Yeah" Dan answered

"Then what are you doing here?"

* * *

Blair pushed him away and he was left all alone in Brooklyn. Nate wasn't speaking to him, but agreed to tell everyone he received the black eye from Nate's elbow while playing soccer. His home life wasn't any better as his father grounded him for a month and took every electronic device other than his cellphone away.

So when Friday came around, it didn't come as a surprise that he was spending the evening writing in a notebook with nothing but the sounds of the wind and chatter coming from outside his window. It was just like old times.

He received a Gossip Girl alert and reached out for his phone.

_Spotted:_

_**B **__having dinner with __**N**__. With Cotillion around the corner, reconciliation must be in the works for our favorite couple. _

_You know you love me_

_XOXO,_

_Gossip Girl_

He wished it stung, because it would be easier to manage, but what he was feeling was unexpected. The hurt he was feeling made his heart a lot heavier. Dan knew there was no way he would be able to sleep tonight.

He looked through his closet and took out a nice button down before leaving his room through the fire escape. When he reached the sidewalk by his building, he pulled out his cellphone and scrolled through the contacts until he reached the letter C.


	5. Chapter 4

_I'm not surprised people weren't happy with the last chapter because Dan's confession was rather abrupt and it was hard to see coming, but I had hoped the readers would keep in mind that Dan was dumped by Serena the night before. The only thing I can say is that I already know where this story is going and I can't change it, so I hope you will have faith in me and my writing. _

* * *

Chuck destroyed his relationship with Nate and ironically, they're left with each other. It was funny how things worked out, but this was the how the life of a student attending St Jude's functioned. Weeks would pass and so would the friends they've made.

Chuck's limo pulled up curbside in Brooklyn and Dan looked over both his shoulder to ensure he wasn't being photographed for a Gossip Girl post. He sat in the limo to see an ascot scarf wearing Chuck Bass.

"What's with the phone call Humphrey?" Chuck smirked.

"I just want to get a drink" Dan said.

Chuck nodded his head and blew smoke out the window of his limo. There was something eccentric about Chuck. His clothes for one, but there was also his personality to consider. One minute, he gave you a reason to love him, but then there were other times where you just wanted to punch him. If it weren't for his surname, Dan wondered how many people would actually speak to him.

After taking a ride, they left the limo to get a drink from the bar. He already received a Gossip Girl alert of them being spotted having a drink. Dan shook his head at the lack of privacy in his life. Coming into their world made him the center of attention. He knew underneath it all, Serena and Blair loved it, but it was something he never wanted or enjoyed.

He took a sip of his whiskey and felt his throat burn. He coughed a little and saw Chuck looking amused with the trouble he was having as they sat next to each other on barstools.

Dan looked around and found the bar to be very high end. Most of the women were at least in their early twenties and the men looked like different hair styled Chuck and Nate's.

He looked down to his shot glass and decided to go for it. He took a shot of whiskey and slammed his hand over the granite counter from the feel of letting the liquor burn down his throat.

"Fuck!" Dan yelled and began coughing a little, covering his mouth with his hand.

Chuck arched a brow. "Do you want another one?"

Dan shook his head and was grimacing. "No"

He realized that this was a bad idea and he wasn't sure he could take another shot.

"They make it look so much easier in the movies" Dan said

"It is easy. You're just virgin to everything Humphrey" Chuck responded and ordered another shot for Dan. "I'm rather surprised you were able to hold Blair's interest"

Retorting back was his first thought, but instead, he chose to take another shot of whiskey and ignore Chuck's lewd comment.

Chuck's hand slid over to his drink and when he lifted it off the top of the bar, it revealed a white pill with a black star.

Dan looked over to Chuck. "What is this?"

"Why don't you take it and find out?"

Dan slid the pill back over to Chuck. "No thanks"

That trademark and smirk mixed with a light laugh appeared on Chuck's lips and it made him look insane, but evil as well. Chuck popped the pill in his mouth and took a shot of his drink.

'You're crazy" Dan said

Chuck leaned in and he could smell a trace of alcohol and smoke. "I'm a 17 year old millionaire. How else am I supposed to have fun?"

Dan swallowed and nodded. He then looked away and chugged his shot, feeling a little scared at the prospects for tonight.

* * *

Blair had been asked to Cotillion by Nate, which was her dream before junior year started, but now her mind had been on other things. Things she didn't want to think about and felt embarrassed to even acknowledge.

She was hosting a party for the evening and it would be simple enough to set up. There would be no catering or theme, just a simple exclusive private school party for her friends. She spent an hour just making sure her hair was perfect and presentable, even after the guests had arrived.

"Have you seen the latest Gossip Girl blast?" Asks Jenny who was sitting on the edge of the bed in her hand-made dress.

Blair sighed in annoyance, feeling bothered with someone distracting her from the mirror.

Blair looked over her shoulder and presented a fake smile. "No, but I'm sure if it's anything important, it'll be the talk of the party."

Jenny took it the wrong way and bit her tongue. It was moments like these Blair had doubts about the girl. There were times when she would speak her mind, but there were other times were she would resort back to being the shy girl from Brooklyn who was just happy to be in her mere presence.

"Spill it little J"

"Dan was spotted with Chuck leaving a bar" Jenny told Blair.

Blair pursed her lips smiled. "Good for him" Blair said a little too excitedly, but it was evident there was more pain then actual pleasure. "I'm sure Chuck will show him a good time"

"Blair" Jenny tried to interrupt.

"Why would me and Serena be enough for him? Why not just sleep with the rest of Manhattan" Blair vented and then huffed out a breath that indicated her frustration. She let out too much of her feelings and knew it was time to take control of the situation. "Anyways, we should be heading downstairs. I'm sure Serena is expecting me"

She waved Jenny off, indicating her need for some privacy. Jenny scurried off and she was left alone to head for the bathroom. Two fingers went down her throat and the feeling of control was revived.

* * *

Dan entered Blair's foyer to see overly-dressed teens feeling a little tipsy. With Chuck by his side, it didn't come as a surprise that everyone's eyes were on them. Cellphone's were pulled out to take pictures and post on Gossip Girl and it made him realize these people had nothing better to do with their lives.

He leaned his shoulder against the doorframe of the living room and watched a leg crossed Blair chatting with her friends by the sofa. Unlike the others, she was holding a champagne flute of some fruity drink. She always liked to class things up.

"There is no one better to be single with then Chuck Bass" Carter said.

Dan looked over his shoulder to see a dirt blonde slightly older looking boy handing him a drink. The front of his hair had a little flip with gel.

"That's the word on the street" Dan replied

Carter stuck his hand out. "Carter"

"Dan"

Carter looked over his outfit with a smirk. "A bit under-dressed aren't we?"

Dan furrowed his brows and looked as though he was trying to recognize Carter from somewhere. "I'm sorry, who are you again?"

"Serena's date"

Serena sure moved fast was the first thought to cross his mind. They both did in actuality and it was probably a sign. He wanted to laugh at himself for letting the guilt of sleeping with Blair slowly eat at him.

"Carter. I'm not happy to see you, but I'm sure everyone else is" Chuck said as he stepped into their conversation.

"Chuck Bass and the guy from Brooklyn. That's quite a duo" Carter replied as his went back and forth in between Dan and Chuck.

Dan's lips curved slightly. "We're actually each other's back-up plan"

"Exactly. It's not that we want to spend time with each other. It's just that we don't have a choice" Chuck explained.

"And right now" Dan looked over his shoulder to see Serena and Blair in the living room giggling. "Everyone hates me"

* * *

"I heard he struck gold on the gambling tables of London" Kati told the girls.

"Na-ugh, he was stranded on an Island" Kati replied and straightened out the hem of her dress, sitting on the sofa next to Blair.

Serena laughed and decided to interject. "Oh you girls are just too gullible. What actually happened was that Carter didn't accept his parent's trust fund and left to travel. He wanted to find himself"

Blair scrunched her nose in distaste. "Well whatever it was, he smelled terrible and it looked as though he hadn't showered in months"

Serena looked over to the boys standing by the doorway of the living room. Carter sure did clean-up nicely, but her attention wasn't on her date, it was on Dan. The thought of Chuck and Dan spending time together didn't sit well with her.

"So how is he in bed?" Blair interrupted her focus on Dan.

"I haven't slept with him yet" Serena answered.

"Sorry S, but I'm having trouble believing you. It's been a week and we all know you have a 3 day rule" Blair teased and smirked. The girls giggled but Serena glared at Blair. "What's not to like S? He's good looking, rich, and has somewhat of a bad boy quality to him"

Before Serena could reply, she received a Gossip Girl alert.

_Hey Upper East Siders, Gossip Girl Here:_

_With cotillion only a week away, the rumors are swirling. And boy do I have a good one tonight. __**S **__dumped __**D **__but we never knew why. The word out there is __**D **__cheated on __**S **__with a mystery girl. What __**S **__doesn't know is that her ex wasn't very heartbroken….I'll let you fill in blanks._

_You know you love me_

_XOXO,_

_Gossip Girl_

Serena's jaw clenched and she tilted her chin up to look at Dan who was reading the blast from his cellphone. His jaw dropped and his eyes left the phone screen to meet Serena's. It was very rare for someone to ruin her mood, but Dan affected her in ways others couldn't.

She excused herself from the girls and pulled Dan aside to the isolated hallway that had the library on one side and the door to Eleanor's office at the end.

"What the hell is this?" Serena whispered harshly and shoved her phone in his face.

Dan's head fell back against the wall and she heard a sigh leave his lips. "I really was hurt when you dumped me"

Her eyes crinkled in a questionable manner. "So the blast isn't true?"

"Not entirely. I think what the Gossip Girl meant by the blast was that I've fallen pretty hard for someone else" Dan confessed as the back of his head left the wall and his concerned eyes met hers. "I slept with her after you broke up with me"

Her lower lip began trembling as she tried to control the tears from welling out. Two months they had dated, and nothing had ever compared to how she felt when she was with him. So when he told her he had been inside someone else, many emotions were felt; Stupidity for one, and a crack in her heart as another.

"I thought you loved me" Serena said softly

Dan swallowed hard. "I thought I did too"

"You were supposed to be the good guy"

"I'm trying to be" Dan reasoned

"Then why do I feel like this!" Serena snapped, leading Dan to recoil.

She bit her cheeks and inhaled through her nose before leaving him alone in the hallway.

* * *

Dan searched and his eyes scattered around looking for Blair. Serena was heartbroken and the only thing left in his control was to try and patch things up with Blair.

He looked everywhere and was pulled in to be sandwiched by two girls dancing. He somehow got away and headed up the staircase to Blair's room. Outside her door, he heard chatter that was breaking up due to the door in-between them.

Dan sighed and decided to knock on her door lightly only for Kati to open the door. Her nose scrunched in disgust when she saw him.

"Is Blair in there?"

Kati opened the door a little more and he saw Blair standing with a group of girls and arching a brow. Her dress was black as usual. It seemed like a theme for which he did not understand. She was holding a confident smirk and there was façade of him having no effect on her.

"If you're looking for Serena, she left with Carter" Blair smirked and sat on the ottoman touching the end of the bed. "But I suppose it's for the best. Unlike you, Carter meets her standards. Don't you agree?"

She crossed her legs and straightened out the hem of her dress before looking up and raising her brows expectedly, waiting for an answer.

His throat tightened and he felt at unease being in the glowers of the girls in Blair's bedroom. It was difficult for him to come up with words because his mind kept drifting off to last week when they were alone.

"I was actually looking for you" Dan said. His words caused a little stir as the girls began looking at each other. "It's about Serena"

Blair dismissed the girls and shut the door. He heard a click from the lock and both her hands remained behind her as her back pressed against her door.

"So Humphrey, what about Serena do we need to discuss" Blair asked, not acknowledging their past.

He stepped closer hesitantly and tried to ignore how unsettling it was being Humphrey again. He came just close enough to catch the hint of her Chanel No. 5 but surprisingly, she looked unaffected with how close he was.

"This is the first time in a week I have you cornered alone" Dan said and his lips curved in small manner. "You never let me explain"

"There is nothing to explain. I'm not going to be in another relationship with someone who thinks about Serena when he's with me" Blair told him

"How can I think about Serena when I'm busy listening to your wit?" Dan asked and held a smug grin.

The corners of her lips were on the verge of curving. "Go on"

"I can't switch my feelings off right when we start spending time together. You have to give me time to get over her, and I think the same goes for you with Nate" Dan explained.

"It's not about your feelings. It's about who you want"

"And I want you" Dan replied assuredly.

Everything about Blair was attractive. He couldn't fine one part of her he would change. It was one of those things where something about her just clicked with him. They were so alike, yet so different and that made for a perfect balance.

"If you had read my birthday gift, you would know that," Dan told her. "You by yourself have ruined Serena for me. I can't go back"

Blair looked away but her eyes displayed fear. A frown appeared on Dan's lips when it came to his mind that he had hurt her pretty badly. He leaned in and pressed a soft kiss on the corner of her lip. She still wouldn't look at him, so he went on and cupped her hips. When he lifted her up, she naturally crossed her ankles and he repeatedly pressed kisses on from her cheek to jaw.

Dan carried her to the bed while she continued to be put out a cold front by not meeting his lips. Persistence was the only way to win her over.

"Blair" Dan called for attention as she had him straddled on the bed. She finally met his eyes, but gave him a sharp look. He cupped her cheek and started stroking her jaw with his thumb leading her face to soften.

He decided to be gentle and slow with her tonight. He carefully took her dress off while pressing soft kisses on her collarbone. Intimacy was what he was aiming for and it was why he made sure to stay above her when they were connected. His eyes never left hers and he wanted to make sure they were looking at each other when they climaxed.

* * *

They stared at each other as they were sitting in her town car. Blair left her party and gave him a ride back to Brooklyn. She was leaning against her shoulder while holding a small smile as her body was turned to him.

This was different from before. For the first time, it wasn't just sex. He put himself completely out there and she didn't deny him. It was as exciting as being on a great first date because the future looked so bright.

"I'm in trouble" Blair said with a smirk and Dan chuckled knowing how she feels. "What am I going to do with you?"

She bit her lower lip and continued to hold his gaze. Their stare was soon broken when Blair's cellphone began ringing. She looked at the phone screen and silenced her phone.

"Who was that?"

Blair shook her head lightly and closed her eyes, trying to wave it off. "My brother Tyler"

He looked at her quizzically. "You have a brother?"

Blair smiled at the thought of Tyler. "Yeah; He's 12 and attending some boarding school in Maine. But he'll be back in New York for the holidays"

"I'd like to meet him, but I'm unsure if I'll be off groundation by then" Dan said

"Do you know how long you're in for" Blair inquired.

"Well it just got extended after tonight. So five weeks" Dan answered and crinkled his brows as he calculated the weeks.

The town car stopped and they had finally reached his loft in Brooklyn. Blair grasped onto his collar and pulled him in for a soft chastise kiss on the lips.

She pulled away and stared into his eyes. "I'll see you in school tiger"

Blair let go of his collar and he left her car with a wide grin on his face.

* * *

_I really hope you guys enjoyed this chapter because I'm really nervous after the last chapter. _


	6. Chapter 5

_The next chapter will be the last of this story, which might seem sudden, but I do plan on writing sequel and there will be more than just one. As for the dislike of Dan, I can't agree more. It's hard to find someone in the middle of a love triangle likeable._

_Just as a warning, the ending to this chapter is very shocking, but hopefully people aren't too upset. On a side note, this chapter is rated very M._

_Again, as always, thank you for the reviews and words of encouragement._

* * *

For the first time in Dan's life, he knew what it felt like to be blind. The only sound he could hear was breathing. The scent of Chanel No. 5 was slowly hinting up to his nose as her warm skin drew closer. He tried to maneuver his wrist away, but the knot was too tight and he had lost his freedom. Pure torture was the only thing he could foresee.

A tongue was the first thing he tasted. In response, he stuck out his tongue to meet hers, and they rolled against each other. Soon, her lips joined in and the nipping of his lower lip ensued while feeling her bare breast rubbed against his chest. He forever hated his briefs tonight, as they were in-between him and her.

Five weeks had passed since he had a moment alone with Blair, and it seemed he would have to endure a little more pain.

Her lips left his and he tried to protest by moving his head up, but none came of it as he was tied to the bed, which only irritated him further.

It remained quiet for a fragment of time, but then he heard a bottle being squeezed.

His tongue darted out and an erect nipple teased it. Her nipple was sticky but sweet and honey was what came to his mind.

She moaned at the sensation of him sucking and biting on her breast, relishing the honey on her milky skinned breast. He could only imagine her shutting her eyes and rolling her head back. This god forsaken blind-fold was going to be burned as soon as he was set free. All he wanted to do was touch her, but it was impossible to do so.

After being fed an assortment of fruits mixed in with her lips, she started setting a trail of kisses all the way down to his abdomen. Her little fingers started shrugging off his briefs and the tip of his length felt the relief of being out in the open.

An embarrassing groan left his lips when she began placing soft chastise kissing along and on the tip of his cock. Her lips left, but her hand worked his hard-on and soon, she wrapped her lips around it. The feel of her throat was driving him insane. Not being able to see how she was making him feel was unjust.

Blair left his eight inches and a smirk formed on her lips as her hand began working on his length again. He seemed to be in so much agony that she decided to let him have his way and release him.

She took his blindfold off, she licked her lips when she saw the fire in his eyes. This was exactly what she wanted. As soon as she untied him, he turned her around and made her face the headboard.

"You just made a big mistake," Dan whispered in her ear and her lips curled into a devilish smile.

There was nothing better than being on her knees and having Dan fuck her from behind. The tip of his cock teased her opening and her jaw clenched as she waited in anticipation, only holding on to the headboard tighter.

Soon, she took control and grabbed his length from behind, forcing it to ease in. They moaned together in unity when he entered her fully.

There wasn't much air left in the room once he began thrusting his hips, slow and hard. The only sound resonating in the room was their skin slapping together and their heavy breathing. She was more panting than anything else.

"Oh fuck yes Dan"

She pressed her back against his chest, clenching her jaw, and letting him grasp onto her breasts as he pounded into her. His lips were nearing hers and she turned her head to give him open mouthed kisses. The sweat from her back was mixing in with the sweat on his chest and it only heightened her feelings at the moment.

Blair couldn't help but whimper to his bare cock sliding into her slickness. It was so difficult to think. She never thought sex could be this mind-numbingly good. The only thing she could ask for was a mirror in front of them so she could watch him.

She placed her hands over his, which were grasping on to her breasts. "Tighter"

She wanted to be his and sometimes she it would be difficult for him to understand that.

"Harder" Blair demanded, which only made the headboard banging against the wall more noticeable.

Her moans were getting loud as she came closer and closer to her peak. She went back down and started teething the bed in hopes of stopping the cursing from leaving her mouth. Her walls were clenching with his continuous pounding and she was close.

With one last thrust, she moaned loudly and finally let go. Her body shuddered violently and she was grasping onto the bed.

She fell on his bed from not being able move, but it was a problem for Dan since he hadn't found his release yet. The gentleman he is, he slid to her side and pressed her hips against his length. His arms wrapped around her waist and he slipped into her from behind.

His forehead was pressed against the back of her head and he was moving slowly, but the way he moved his hips only produced another build up.

"You're good. So good" Blair rambled off, gasping for air and feeling the damp hair over her eyes and lips.

As soon as she started moving her hips around his length, her ear was filled with a pleasant groan. She met his groan with a moan escaping her lips. The feel of his lips connecting to her neck was driving her to pure ecstasy alone.

Dan used the arm wrapped around her waist as leverage to thrust faster. Her head rolled back and his lips began kissing her clenched jaw.

"I've never felt so good" Dan said softly and slowed down his pace.

Her eyes shut to his words and she let them slowly find their release together.

Panting heavily and relishing the afterglow, she let out satisfied gust of air and enjoyed the feeling of the soft kisses Dan was placing on her cheeks and jaw as she laid back against his chest. Being wrapped around his arms and kissed in an affectionate manner was different for her. She secretly enjoyed it, but would never admit to such a thing, so she would remain quiet and hope he would continue holding her this way.

* * *

The door to the fridge opened and a wide variety of food was waiting to be picked at. There were appetizers that looked delightful but more suited for Blair. Of course there were meals as well, like pasta and steaks waiting to be grilled. Dan reached for the marinated steak and placed it on the grill. To his surprise, Blair had an indoor gas grill in her kitchen which was mind blowing and maybe even illegal.

"What are you doing?"

Dan looked over his shoulder to see a brunette boy standing by the island and wearing a red smoking jacket.

"You must be Tyler" Dan said

Tyler was just as pale as his sister. He's a Waldorf, so of course he had the same thin frame, but good shoulders like his mother. Just like most residents of the UES, his hair was short and clean.

Dan left the grill and stuck his hand out. "I'm Dan"

"Hi" Tyler replied and headed towards the fridge, leaving Dan to hang out dry. "What's your last name?"

"Humphrey" Dan answered and watched Tyler pull out a small plate of chocolate cake.

A crease formed in-between Tyler's brows as he strode his way over to the island. "I'm sorry, but I've never heard one word spoken about that name. Did your family just move here?"

"I'm from Brooklyn" Dan clarified.

He received the same response as he always would. A scrunch of the nose.

Blair sniffed to figure out what was reeking out to her living room. "Is someone grilling?" She stepped into the kitchen and saw smoke coming in from the background. "I said a snack Dan!"

She shook her head and turned on the exhaust fan above the grill.

"Is mother okay with you seeing him?" Tyler asked.

"She isn't exactly ecstatic over it if that's what you're asking" Blair pursed her lips and presented a fake sweet smile.

It was pretty remarkable to see her still have that sarcastic bitchy attitude towards her brother.

In the end, Dan had his way and enjoyed some steak. The one thing he learned was that Tyler was clearly impressed with his sister. Tyler looked up to her in ways Jenny didn't look up to him which made him question his relationship with his sister.

They started going on about some Christmas dinner and Dan knew that was his cue to leave. Blair's penthouse was going to be filled with the Archibald's and Van Der Bass's after the day of Christmas and that was not something he considered a good time.

The last five weeks were the most peaceful weeks he's had in a while. He doesn't like Nate very much and it's the same way for Nate. Serena had been avoiding him since the Gossip Girl blast which he completely understood. But the most shocking thing was that Chuck was probably his best guy relationship at the moment and it was a tad unsettling.

Before Blair could invite him, because he knew it was coming, he placed a kiss on her cheek and left for the loft in Brooklyn.

* * *

Serena's little fingers curled around the metal handle of the coffee shop in Brooklyn. She spotted Dan with a green apron behind the counter handing money back and shutting the cash register. When their eyes met, she saw a hint of lip movement from the corner of his lips. It was obvious he was fighting the natural reaction of seeing her.

Placing her bag and jacket on top of the counter, her hips lay on top of the stool and her body is made sure to face him. A trace of Cool Water cologne trailed all the way over to her.

"What's going on" Dan greeted with a smug grin.

Serena looked around. "So this is how people make ends meet"

Dan laughed a little. "I suppose"

As he took an order from a customer, her eyes went to the menu, but really, she was thinking of a way to breach the subject. Five weeks had passed and there wasn't even a whiff of this girl Dan had feelings for. Something had been obviously missing.

After handing the customer her order, Dan laid his attention solely on her. "What are you doing here?"

"I just thought it had been a while since we had really spent any time together" Serena said and raised her eyes off the menu. "Obviously I was upset at first, but I think we can at least try and be friends. Don't you agree?"

She was pleased to see the little smile on his lips.

"Yeah, of course"

Serena smiled brightly and clapped her hands together excitedly. "Yay! We could start with this weekend. I'm bringing Carter to Eleanor's dinner and you should bring a date as well"

Dan didn't get a chance to respond as his eyes drifted off to the front door. A sigh left his lips and a frown appeared. She looked over her shoulder to see Nate and Chuck entering the coffee shop.

"Daniel, may we borrow some time off that lunch break of yours?" Chuck asked

"How polite of you to ask. You usually just do or expect" Dan responded not looking pleased to see them.

There was unwarranted tension Nate and Dan as of late. Her first thought was it may have been over soccer, but it was clearly bigger than that.

"Carl, I'm taking a break" Dan told his manager and tossed his apron on the counter. "I'll catch you later Serena"

In a brisk, Dan left with Nate and Chuck into the limo. All Serena wanted was to know what was going through his head. They ended so abruptly, going from on top of a mountain to hitting the ground without ever feeling the air against her hair.

A curly haired Vanessa gave Serena a sad smile and came over in her green apron.

"Hey Vanessa" Serena said and her voice wasn't hiding the disappointment.

Vanessa leaned over the counter and used her elbows as leverage to prop her head. "You look sad"

"I'm just confused"

"Maybe I can help" Vanessa replied leading Serena to lift her eyes to meet Serena's. "Dan told me what happened and I would typically stay out of it, but this is a rare case"

"What do you know?" Serena asked

"I read some of Dan's latest pieces of writing and Blair was the center of it all" Vanessa told Serena but looked a little frightful of Serena's response. "I thought you deserved to know you're best friend might be going behind your back"

"Does Dan know you know?"

Vanessa shook her head. "No, I found them while he was in school"

Serena grabbed her purse. "Thank you Vanessa"

* * *

Chuck pulled out a lighter to light his cigar in the limo. He looked at Dan with a smirk and blew out puff of smoke his way.

"I hate to admit this, but I may require your services Humphrey," Chuck said.

"You really know how to make a boy feel all tingly" Dan replied dryly but couldn't fight his lips from curling.

The look Nate was giving him wasn't doing them any favors. There were times where he considered punching Nate and dueling it out with him just to get it over with.

"Do you know what happened with Carter?" Nate asked

Dan nodded in response. Chuck caught him up on how they were played by Carter during a poker game. Carter had a troubled past and was in debt with some serious people. That was where Nate came along. The blonde had money and was the brightest boy in the world.

"Serena tells us you're a good poker player" Chuck said.

When a person doesn't have friends, they have time to learn new skills. Writing was his passion, but being able to play poker was his gift. He spent the past few years illegally gambling online, and made good money doing it.

"We both know Serena can go overboard with complements" Dan deflected looking out the window and trying to play it cool when he was really pissing himself. If he caused any more trouble, he swears his dad was going to send his ass to public school.

Chuck's eyes narrowed a little and his cheekbones rose. "Don't play coy with me Humphrey"

Dan sighed and rubbed the back of his neck. "What do you guys want?"

Nate scooted closer and leaned in. "Carter's going to be in a high stakes poker game tonight and if we work together and take him out, he'll be back in debt"

"Of course we'll stake you in, but you must come to Waldorf's dinner tonight. Once dinner is over, we'll sneak out and head for the Ritz where the poker game will be played" Chuck added.

Dan rubbed his forehead and started going into deep thought, thinking of what to do, because when it came down to it, he would always have Nate's back.

* * *

Reaching for the suit his grandfather gifted him, Dan couldn't believe he was going through with it. He carefully put the suit on after showering and headed for the kitchen to see his father waiting for him. Rufus was leaning against the island countertop arms folded across his chest.

"And where are you heading on the day of Christmas?" Rufus asked and then gestured him to take a seat on the couch.

Dan walked over to the couch and Rufus sat on the edge of the coffee table, leaning in.

"Eleanor Waldorf is hosting a Christmas party and I was thinking of joining Jenny" Dan told Rufus.

"See, I can understand Jenny attending, but why on Earth would you be?" Rufus questioned and looked as though he wasn't buying it.

"I'm kind of dating Blair" Dan said with a worried expression on his face.

Rufus's face went from serious to amused. "95 pounds of girly evil Blair?"

"Yeah"

"Wait" Rufus threw both his hands up to halt the conversation. "Before we go any further. Are you telling me Serena is okay with this?"

Dan looked away and Rufus read right through him.

"I'm really getting tired of this Dan. I know you're having a difficult time with Allison leaving, but that doesn't mean you should use it as an excuse to turn into Serena and her friends" Rufus lectured as his smile faded. "You are not like them. You have principals"

"So I shouldn't go?" Dan asked hesitantly.

Rufus shook his head thoroughly. "No, you should. You've been responsible these past few weeks and deserve to have some fun, but that doesn't mean you should let girls like Blair or Serena change you"

Dan nodded. "Alright"

Rufus's lips curved slightly and he patted Dan's shoulder. "Alright"

* * *

After collecting her thoughts and making a decision on what to wear for the dinner, Serena left for Blair's. When she stepped into Blair's room, she saw her friend having a conversation on the phone. It was clear Kati was on the other side being scolded by Blair for allowing Nelly to be on the list of invitations to the New Year's party at the Palace.

Serena put two and two together. Nelly had a crush on Dan and Blair was marking her territory. She always thought Blair's discourteous behavior towards Nelly was based solely upon academic competition, but it became evident that wasn't the only reason.

A sigh left her lips and she couldn't believe how much of a fool she was. Everything was right in front of her and what made it more difficult to believe was how Dan looked past Blair's immaturity.

When Dan was with her, he was judgmental about her world, yet with Blair, it didn't matter. For the past month, there had been something different about Dan. He was calmer and accepting, there wasn't this insecurity of not belonging.

As she sat on the end of the bed, waiting for Blair to finish her conversation, she couldn't help but be frustrated. Her eyes ventured off to Blair's cabbage patch doll and her eyes widened when they landed on Cedric sitting beside Holly on the shelf.

Blair stuck one finger out in Serena's direction as a request to wait. "Kati, I have to go, Serena's begging for attention" Blair ended the phone call and tossed her phone aside while holding a smirk. "Where's Carter?"

"He couldn't make it; He said he was spending his night with family"

Blair stood off the bed and made her way over the mirror. "Good for him I suppose"

Blair was wearing a low cut black dress that fell to her knees and had a sparkling sliver ribbon tied around the waist. She watched the brunette spin around and looked over herself in the mirror. The cool and calmness of Blair was trying.

"I'm considering forgiving Dan and asking him to take me back" Serena said, wanting to read Blair's reaction.

To her surprise, there wasn't much of a reaction to Dan's name. Blair went on, playing with her dress a little and making sure she didn't look anything less than perfect.

"How unfortunate, I thought the days of speaking about Cabbage Patch were behind us" Blair turned around to face Serena and placed a hand on her hip. "But I can't say I'm surprised. You've been leering dear"

Sometimes it was impossible to tell what Blair was thinking and this was one of those times. Her cuts were always on the inside. She knew Blair very well and there were only two ways her best friend would go about it. One was Blair running back to Nate because she was scared of getting hurt by Dan, or she could be keeping her emotions under control and scheming.

Serena was never the type of girl to play games. Rather than making the situation into more of a mess, she decided it would be best if she just confronted Blair, but before she could speak, they heard someone playing the piano downstairs.

Their attention went downstairs and they carefully stepped down the staircase to see Dan playing the piano for Eleanor who seemed filled with merry. It was very rare to see Dan wearing a suit and tie, so when she did, he looked more appealing than usual. Unfortunately, she was falling for him again and the beautiful notes ringing in her ears weren't helping.

Serena glanced over to Blair and there it was; that look. It was clear Blair adored Dan, and the thought of that scared Serena.

When he ended his song, he stood off the bench and bowed to Eleanor, only to hear clapping from Blair's mother, Jenny, and Dorota.

"That was wonderful Daniel" Eleanor applauded.

Dan cleared his throat and used his hand to point to Jenny. "Thank you, but Jenny's the talented one. She can actually sing as well as play the violin"

Eleanor turned her attention to Jenny and Dan coyly walked over to the girls. After he shoved a hand in his pocket, his eyes went to Blair.

"Jenny invited me as her plus one, I hope that's okay" Dan told Blair.

Blair raised her brows and gave him a look of superiority. "You're lucky I'm in a giving mood today"

Dan stuck his hand out for Blair to reach. "Maybe I can make it up to you by giving you a lesson"

There wasn't any hesitation from Blair as she placed her hand on top of his. Serena shook her head and watched them walk over to the piano.

* * *

Blair sat on the bench with the piano in front, listening to Dan's instructions. It was difficult for her eyes to remain open as a trace of his cool-water cologne reached her nose. The heat coming from his skin was making it difficult for her to concentrate.

Dan stood behind her and carefully placed an arm over her shoulders. His fingers were on top of hers, and he was signaling her to follow his lead.

His lips were only inches away from her ear. "That dress looks amazing by the way. You can pull anything off with that creamy complexion of yours."

Blair sharp intake of breath through her nose and let his fingers lead. She slowly followed his lead and started getting excited to the notes they were making together. It was basic, but she was still proud for being able to create such a beautiful sound.

They had to stop playing once her penthouse began filling in with the invitees. Blair didn't feel the need to welcome everyone in since her mother was playing that role. So she spent most of her time with her peers. It didn't go unnoticed that Humphrey was speaking with Chuck and Nate for most of the night. It was making her very suspicious. For the past few weeks, he had spoken very few words to Archibald, yet here he was, having a ball with Nathaniel.

When Dan stepped away from the boys, she pulled him into her secluded hallway, eventually reaching the library. Instinctively, his fingers intertwined with hers and she allowed it, but still gave him a sharp look.

Not letting a second go to waste, Blair asked, "Why is Nate speaking with you?"

Dan leaned in, fighting a smile. "Why? Does it annoy you?"

Blair smirked. "I was rather enjoying the thought of two boys fighting over little ol' me"

Dan bit his lip, looking amused.

Blair grasped onto his collar to tug a little closer. "Tell me" Blair whined and pouted her lips a little, knowing she was being overly dramatic. "I'm dying to know what you three are up to"

A smile broke out from Dan's lips. "This passion for drama is getting a little ridiculous don't you think?" Blair let go of his collar and glared in response, leading Dan sighed dramatically. "Fine, if you must know, we plan on ditching this party to play some poker"

Blair pressed her lips in displeasure knowing he wasn't telling her the whole story, but lucky for him, she would let it go because there were other things they needed to discuss. Her fingers reached in her clutch and drew out a small gift wrapped box.

"Merry Christmas" Blair said

When she handed it to Dan, he looked a little taken back. His fingers worked slowly and she waited in anticipation to see his reaction.

The box unraveled a rusty golden fountain pen, making Dan looked a little clueless as he studied her gift.

"It was once owned by Scott F. Fitzgerald. Some say he wrote notes on The Great Gatsby with it" Blair filled him in and moved over to his shoulder to stare at the pen with him. "I bought you some ink so you can use it whenever you write in that moleskin of yours"

It was the first time she ever saw Dan speechless. His brows were furrowed and he looked to be in deep thought as his hips landed the arm rest of the sofa.

After Dan swallowed hard, he looked up and met her eyes. "Why would you get me this?"

"I thought you might like it" Blair reasoned, feeling shy for the first time tonight.

Fitzgerald was all Dan ever talked about. She found him to be overrated, but a girl could learn to tolerate Fitzgerald if the boy was willing to listen to her praise Aubrey.

Dan stood off the couch. "I love it, but this cost more than a car"

Blair shrugged and smiled a little. "I like you"

"I'm surprised it's this much"

"I don't just sleep with anyone" Blair said

"Gurrrrl, neither do I" Dan joked looking offended leading Blair to giggle.

Dan bit his lip and tried to suppress himself from smiling like a loon. He stepped behind her and leaned close to Blair's ear.

"I don't think I have ever received a better present" Dan whispered and kissed below Blair's ear.

The black dress fell on the floor and Blair turned around, giving him an alluring smile. She tossed her headband aside and pushed Dan onto the sofa.

Serena watched from the little opening from the door to the library. Blair and Dan were kissing each other passionately and it made her stomach churn.

* * *

After spending some alone time with Blair, Dan snuck out of the Waldorf's with Nate and Chuck. They headed for the Ritz and took the elevator up to a 2500 square foot suite. There were barmen making drinks for the players and there was only one table. Two men looked to be in their early thirties while the other man looked like he was in his mid-20's.

He always imagined high school being more like the breakfast club or sixteen candles, but attending Constance and spending his weekend's in the Upper East Side was nothing like those movies. It was difficult to relate to anyone and lonely was the only word he could use to describe his experience.

No one questioned his age and maybe it was because he came with Chuck Bass. He wondered if they will be feeling the same way once he leaves them dry.

It started out slow, everyone checking mostly, not wanting to raise the stakes. Of course the pace of the game eventually started picking up.

Chuck and Nate were bleeding chips but he was going strong and only behind Carter when it was time for a break from the game. Dan took his drink and left for the terrace to have a moment alone.

He wasn't surprised to see Carter following his steps to the terrace.

"I don't like it when people fuck with my shit Dan" Carter said shoving his hands down his pockets and looking out in the skyline. "Why are you helping them?"

Dan's eyes remained out on the skyline of New York City. "I'm only doing it for Nate"

Carter turned over to face him. "I remember being a part of this world. It seems so glamorous that it's impossible to see how toxic it truly is"

Dan looked over to Carter. "Get straight to the point man"

"Chuck and Nate aren't going to last long, which basically leaves you and me with a bunch of pretty good players. We team up, get rid of those players and when it's down to us two, you let me win" Carter told Dan.

"Why would I do that?"

Carter leaned in. "If you let me win, we can split the pot. I get the fuck out of here and you stay here looking pretty"

If executed right, the plan was perfect. It was actually better than winning because he would have to give the money he won back to Chuck. But this way, he looks like he tried, but Carter won and they won't know him and Carter had a deal.

"I see it in your eyes man. You want to get the hell out of here and go to some Ivy League school, but the only way you can attend is if you have money. Otherwise kiss Ivy goodbye and get a full ride to somewhere like BU or NYU" Carter said.

"I don't know if I can do that to them" Dan admitted softly

"From what I heard, Chuck wasn't too kind to your sister. I'd say you were just getting even" Carter disputed.

Dan rubbed his face thinking of his next move. He could take the money and leave New York for good after graduation, or he could be the good guy and remain loyal to Nate.

"So what do you say?" Carter asked with a smirk.

* * *

Blair sighed and flicked the lights off in the dining room. She headed for the foyer only to see Serena sitting on the bottom of the staircase reading the moleskin Dan gifted her on the day of her birthday.

When Serena heard Blair's heels, her attention was gained and her eyes were on Blair.

"We need to talk" Serena said.

* * *

Dan placed the old loose floorboard back and threw a rug over it. He then slid his bed back over it and went back to his desk to study for the SAT's.


	7. Chapter 6

_This is a short but sweet chapter. The story has come to an end and I wanted thank everyone who read through it. Hopefully, you'll be there for the sequel._

* * *

Dan was awoken to the ringing of his phone from a Gossip Girl blast. A groan left his lips as he rolled over and reached for his cell phone.

_Good Morning Upper East Siders,_

_This juicy rumor may be too big of a pill to swallow for some of you just waking up…. Don't say I didn't warn you. _

_Look out **S**, you may have competition for Lonely Boy's heart. Our once Virgin Queen has turned Dark. Tish, tish **B**, don't you know you never sleep with the best friend's ex. _

_Until next time, you know you love me_

_XOXO,_

_Gossip Girl_

* * *

Dan found himself in Blair's penthouse. The sound of silverware was heard, but before he could take a step towards the dining room, Dorota came forward.

Dorota smiled. "Mr. Dan, how nice to see you"

Dan rubbed the back of his head nervously. "Um…Good morning Dorota"

"Ms. Blair and Ms. Serena waiting for you" Dorota said and led him to the dining

The news of Serena being at Blair's made him feel like he on the verge of entering a land mine field. When he reached the dining room, he saw everyone acting civil towards each other. They looked like a family enjoying a quiet breakfast.

"Daniel, why don't you join us" Eleanor offered.

Dan sat down and before he knew it, there was a plate filled with bacon and eggs in front of him. He took a bite out of the bacon and he fought himself not to moan, but couldn't fight his eyes from shutting. There was nothing more he loved then the food in the Upper East Side.

"Enjoying yourself Dan" Blair said, lips pressed thinly in displeasure.

He opened his eyes and nodded, but saw a glimpse of movement from the corner of Blair's lips. The breakfast went by fast and they went over many topics, one being his father. Apparently, his dad was invited to Lily's New Year's Eve party, which was for grown-ups only. Rufus never gave him any hints of knowing Lily so the news came as a surprise.

Right when breakfast was over and Eleanor had left the penthouse, Tyler was ordered to go to his room and he was left alone with Blair and Serena. They sat him on the white ottoman and the feeling of peace and serenity was long gone.

Serena folded her arms across her chest and gave him a hard look. "What's going between you and Blair?"

A crease formed in-between Dan's eyebrows. "Blair didn't tell you?"

"All she said was the sex is good" Serena answered.

Dan looked over to Blair, who had a hand on her hip and was raising both her brows while holding a superior smile. Sometimes he would forget how much of an Ice Queen she truly is.

One thing that surprised him was how calm both girls were with the Gossip Girl blast.

Dan eyed them suspiciously. "How come you guys aren't fighting? It's very unlike you two"

"That's because we've been fighting profusely for the past two days" Serena explained looking tired. Serena sat next to him and turned to face him. "Look, I don't want to lose my best friend over a guy and neither does Blair"

"So we're choosing each other" Blair further explained, lifting her chin high and proud.

Blair felt a sense of power for being the one to break things off. It was better to cut her losses before she got hurt anyway. Fighting with Serena over another boy would just lead to her getting left behind and forgotten about.

Dan nodded and stood off the ottoman. "I understand. I wouldn't want to be the root of a ruined friendship between two people I care about"

Blair softened a little when Dan came close. She watched him reach into his pocket and place the pen she gifted him on her hands. She looked up and met his eyes, frowning a little.

"I think you made the right decision. I gave you a fifty dollar necklace and you gave me a pen worth more than anything in my father's loft" Dan said looking dejected. "I'm clearly not the guy for you"

Dan gave them a sad goodbye look before heading for the elevator and she was left wondering, if he wasn't the guy for her, then why did it hurt so much to see him leave?

* * *

The second semester of the school year had already begun and Dan would summarize it as quiet. Spring was still ways away and he spent most of his free time either helping his father with the gallery, or working for the coffee shop after school to help his father with the bills. The money he had was still under his floorboard, but he didn't plan on using it until he graduated from High School.

"It's weird" Vanessa said using her hand to keep her head up on the counter.

"What is?" Dan asked as he cleaned the cup with his table cloth and stared out the window of the coffee shop.

Vanessa leaned off the counter and turned to him. "You don't seem very affected with being dumped twice within a span of three months"

"That's because Serena and Blair are still friends and happy" Dan explained

Vanessa arched a brow. "And what about you?"

Dan glanced over to Vanessa. "Hopefully, I'll get into Dartmouth"

The door to the coffee shop opened and his lips curled into a smile because his favorite customer had just stepped in. She was wearing shades that covered most of her face and her skin was as white as a princess from a Disney movie. Her hair was a darker shade of brown and she had these unforgettable big blue eyes. After both Serena and Blair left him, he was lonely, but then she came into his life and he didn't feel as friendless anymore. The brunette was so sweet and innocent that he couldn't believe she was from the UES.

"Hey Georgina" Dan said.


End file.
